EP1149892B1 - Oberflaechenaktive zusammensetzung - Google Patents

Oberflaechenaktive zusammensetzung Download PDF

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Publication number
EP1149892B1
EP1149892B1 EP00978068A EP00978068A EP1149892B1 EP 1149892 B1 EP1149892 B1 EP 1149892B1 EP 00978068 A EP00978068 A EP 00978068A EP 00978068 A EP00978068 A EP 00978068A EP 1149892 B1 EP1149892 B1 EP 1149892B1
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EP
European Patent Office
Prior art keywords
compound
surfactant
weight
components
carbon atoms
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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EP00978068A
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English (en)
French (fr)
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EP1149892A1 (de
EP1149892A4 (de
Inventor
Takaya Kao Corporation SAKAI
Makio Kao Corporation TETSU
Makoto Kao Corporation KUBO
Akira Kao Corporation FUJIU
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Kao Corp
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Kao Corp
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/528—Carboxylic amides (R1-CO-NR2R3), where at least one of the chains R1, R2 or R3 is interrupted by a functional group, e.g. a -NH-, -NR-, -CO-, or -CON- group
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/645—Mixtures of compounds all of which are cationic
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2065—Polyhydric alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/46—Esters of carboxylic acids with amino alcohols; Esters of amino carboxylic acids with alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/523—Carboxylic alkylolamides, or dialkylolamides, or hydroxycarboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain one hydroxy group per alkyl group

Definitions

  • the present invention relates to a surfactant composition having an excellent foamability, thickening property, water solubility and stability.
  • a detergent such as a shampoo, a rinse, a solid soap, a body shampoo, a detergent for kitchens, a detergent for clothing and a detergent for dwellings.
  • an anionic surfactant such as an alkyl benzenesulfonate, an alkyl sulfate salt and a polyoxyethylene alkyl sulfate salt.
  • any thereof usually shows its excellent detergency and foaming, there is a problem therein that, when solids, a stain derived from silicone or the like is present, the detergency and foamability significantly lower.
  • a purpose of the present invention is to provide a surfactant composition having an excellent foamability, thickening property, water solubility and stability even within a broad pH range, even in the presence of soil.
  • the present invention provides a surfactant composition
  • a surfactant composition comprising the below shown component (a) and component (b) and a surfactant other than (a) and (b) at the weight ratio of (a)/(b) of from 99.99/0.01 to 80/20 or from 99.9/0.1 to 70/30.
  • R 1 CO- is an acyl group as mentioned above. It is preferably a saturated or unsaturated acyl group having 8 to 18 carbon atoms. It includes for example an acyl group derived from octanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, docosanoic acid, linoleic acid, 2-ethylhexanoic acid, 2-octylundecanoic acid, isostearic acid, oleic acid, coco-fatty acid, a palm oil-fatty acid, a palm kernel oil-fatty acid, a beef tallow-fatty acid, etc.
  • the more preferable is an acyl group derived from octanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, oleic acid, coco-fatty acid, palm oil-fatty acid, palm kernel oil-fatty acid and beef tallow-fatty acid.
  • these acyl groups that containing not less than 50 % by weight of acyl groups derived from fatty acids having 12 to 14 carbon atoms is preferable. More preferable is that containing 40 to less than 100 percent by weight of acyl groups derived from fatty acids having 12 carbon atoms.
  • R 2 is a linear or branched alkyl group having 1 to 3 carbon atoms, preferably methyl group or ethyl group. Methyl group is in particular preferable.
  • R 3 is a linear or branched alkylene having 1 to 6 carbon atoms or an alkenylene group having 2 to 6 carbon atoms. It is preferably a linear or branched alkylene group having 2 or 3 carbon atoms.
  • the component (a) includes, for instance, N-(2-hydroxyethyl)-N-methyl octanamide, N-(2-hydroxyethyl)-N-methyl decanamide, N-(2-hydroxyethyl)-N-methyl dodecanamide, N-(2-hydroxyethyl)-N-methyl tertadecanamide, N-(2-hydroxyethyl)-N-methyl hexadecanamide, N-(2-hydroxyethyl)-N-methyl octadecanamide, N-(2-hydroxyethyl)-N-methyl-coco-fatty carboxamide, N-(2-hydroxyethyl)-N-methyl-palm kernel oil-fatty carboxamide, N-(2-hydroxypropyl)-N-ethyl dodecanamide, N-ethyl-N-(2-hydroxypropyl) oleamide and N-ethyl-N-(2-hydroxypropyl) isostearamide.
  • a method for producing the component (a) is not particularly limited. For example, it can be produced by a condensation reaction or a de-alcohol reaction of a fatty acid or a lower alcohol ester of a fatty acid with an alkanolamine, a reaction of a fatty acid halide with an alkanolamine in the presence of an alkaline catalyst, an ester-amide exchanging reaction (an aminolysis) between fats and oils and an alkanolamine or others.
  • the product obtained by such a method may often contain small amounts of fatty acids, inorganic salts, glycerol and the like, but they does not at all affect properties of the product.
  • the component (b) is selected from the compounds represented by the above-mentioned formulae (II) and (III), respectively. It is not necessarily single, but plural species may be mixed.
  • R 1 CO-, R 2 and R 3 of the formulae (II) and (III) have the same meanings as those of the formula (I) .
  • R 1 , R 2 and R 3 may be the same as or different from one another.
  • the compound represented by the formula (II) includes, for instance, N-octanoyl-N-methylaminoethyl octanoate, N-octanoyl-N-methylaminoethyl decanoate, N-octanoyl-N-methylaminoethyl dodecanoate, N-octanoyl-N-methylaminoethyl tetradecanoate, N-octanoyl-N-methylaminoethyl hexadecanoate, N-octanoyl-N-methylaminoethyl octadecanoate, N-dodecanoyl-N-methylaminoethyl octanoate, N-dodecanoyl-N-methylaminoethyl decanoate, N-dodecanoyl-N-methylaminoethyl
  • Examples of the compound represented by the formula (III), for instance, include 2- (methylamino) ethyl octanoate, 2-(methylamino)ethyl decanoate, 2-(methylamino)-ethyl dodecanoate, 2-(methylamino)ethyl tetradecanoate, 2-(methylamino)ethyl hexadecanoate, 2-(methylamino)ethyl octadecanoate, 2-(methylamino)ethyl oleate, 2-(ethylamino)ethyl octanoate, 2-(ethylamino)ethyl dodecanoate, 2-(ethylamino)ethyl tetradecanoate, 2-(ethylamino)ethyl hexadecanoate, 2-(ethylamino)ethyl octadecanoate, 2-(e
  • the blending ratio of the component (a) to the component (b), the weight ratio of (a) / (b), is from 99.99/0.01 to 80/20 or 99.9/0.1 to 70/30, preferably from 98/2 to 90/10 in view of foamability, thickening and stability.
  • the compound (I) is preferably 80 to 99.99 % by weight to the sum total of them, more preferably 90 to 98 % by weight.
  • the compound (II) is preferably 0.01 to 20 % by weight, more preferably 2 to 10 % by weight.
  • the compound (III) is preferably 0 to 5 % by weight.
  • a very high foamability and thickening property can be exhibited in the present invention by combining another surfactant (hereinafter, referred to as "other surfactant") than (a) and (b) with (a) and (b).
  • the total amount of the components (a) and (b) of the composition of the present invention can be optionally selected, depending upon characters of the other surfactant.
  • the blending ratio of the components (a) and (b) in total to the other surfactant is preferably from 0.5/99.5 to 50/50 by weight.
  • the other surfactant used in the invention may be at least one selected from a sulfate-based or sulfonate-based surfactant such as an alkyl sulfate, a polyoxyethylene alkyl sulfate and an alkylbenzene sulfonate, an amine oxide such as an alkyldimethyl amine oxide and amidopropyldimethyl amine oxide and an amide group-containing betaine such as amidopropyl dimethylcarbobetaine.
  • a sulfate-based or sulfonate-based surfactant such as an alkyl sulfate, a polyoxyethylene alkyl sulfate and an alkylbenzene sulfonate
  • an amine oxide such as an alkyldimethyl amine oxide and amidopropyldimethyl amine oxide
  • an amide group-containing betaine such as amidopropyl dimethylcarbobetaine.
  • One or two or more can be used
  • the surfactant composition of the present invention can be improved in viscosity by further containing glycerol.
  • the amount of glycerol to the sum total of the components (a) and (b) and the amount of the surfactant other than the components (a) and (b) is preferably not more than 20 % by weight, more preferably from 0.01 to 15 % by weight.
  • the blending ratio of the sum total of the component (a), the component (b) and glycerol to the other surfactant is preferably from 0.5/99.5 to 50/50, more preferably from 1/99 to 25/75 by weight.
  • Glycerol may be added separately. It may contain that produced in the syntheses of the component (a).
  • the surfactant composition of the present invention can exhibit desired performances such as foamability and thickening property at a pH of 4.0 to 11.0. It is useful as the base for a detergent.
  • surfactant compositions having the formulations as shown in Table 1 were prepared and tested in foamability in the below mentioned method. Results are shown in Table 1.
  • surfactant compositions having formulations as shown in Table 3 were prepared. The viscosity thereof was determined at 25 °C with an ordinary Brookfield viscometer. Results are shown in Table 3.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)

Claims (5)

  1. Tensidzusammensetzung, umfassend die unten gezeigte Komponente (a), die unten gezeigte Komponente (b) und ein anderes Tensid als (a) und (b) bei einem Gewichtsverhältnis von (a)/(b) von 99,99/0,01 bis 80/20:
    (a) Verbindung mit der Formel (I) (nachfolgend Verbindung (I)):
    Figure imgb0010
     worin R1CO- eine gesättigte oder ungesättigte Acylgruppe ist, die 6 bis 24 Kohlenstoffatome aufweist und eine Hydroxygruppe haben kann, R2 eine lineare oder verzweigte Alkylgruppe mit 1 bis 3 Kohlenstoffatomen ist; und R3 eine lineare oder verzweigte Alkylengruppe mit 1 bis 6 Kohlenstoffatomen oder eine Alkenylengruppe mit 2 bis 6 Kohlenstoffatomen ist;
    b) zumindest eine Verbindung, ausgewählt aus der Verbindung mit der Formel (II) (nachfolgend Verbindung (II)) und der Verbindung mit der Formel (III) (nachfolgend Verbindung (III)):
    Figure imgb0011
    Figure imgb0012
    worin R1CO-, R2 und R3 die gleichen Bedeutungen wie oben aufweisen und R1, R2 und R3 gleich oder verschieden voneinander sein können.
  2. Zusammensetzung nach Anspruch 1, worin die Mischungsverhältnisse der Verbindungen (I), (II) und (III) zur Gesamtsumme von diesen 80 bis 99,99 Gew.% der Verbindung (I), 0,01 bis 20 Gew.% der Verbindung (II) und 0 bis 5 Gew.% der Verbindung (III) sind.
  3. Zusammensetzung nach Anspruch 2, worin das Mischungsverhältnis der Gesamtsumme der Komponenten (a) und (b) zu dem anderen Tensid als den Komponenten (a) und (b) von 0,5/99,5 bis 50/50 ist, bezogen auf das Gewicht.
  4. Zusammensetzung nach einem der Ansprüche 1 bis 3, umfassend Glyzerin in einer Menge von 20 Gew.% oder weniger zur Gesamtsumme der Komponenten (a) und (b) und dem anderen Tensid als den Komponenten (a) und (b).
  5. Zusammensetzung nach Anspruch 4, worin das Mischungsverhältnis der Gesamtsumme der Komponenten (a) und (b) und Glyzerin zu dem anderen Tensid als den Komponenten (a) und (b) von 0,5/99,5 bis 50/50 ist, bezogen auf das Gewicht.
EP00978068A 1999-12-01 2000-12-01 Oberflaechenaktive zusammensetzung Expired - Lifetime EP1149892B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP34164999 1999-12-01
JP34164999 1999-12-01
PCT/JP2000/008539 WO2001040421A1 (fr) 1999-12-01 2000-12-01 Composition de tensioactif

Publications (3)

Publication Number Publication Date
EP1149892A1 EP1149892A1 (de) 2001-10-31
EP1149892A4 EP1149892A4 (de) 2004-06-02
EP1149892B1 true EP1149892B1 (de) 2007-04-04

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP00978068A Expired - Lifetime EP1149892B1 (de) 1999-12-01 2000-12-01 Oberflaechenaktive zusammensetzung

Country Status (5)

Country Link
US (2) US6407054B2 (de)
EP (1) EP1149892B1 (de)
CN (1) CN100372919C (de)
DE (1) DE60034215T2 (de)
WO (1) WO2001040421A1 (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4823430B2 (ja) * 2001-03-28 2011-11-24 花王株式会社 界面活性剤組成物
JP4712224B2 (ja) * 2001-05-24 2011-06-29 花王株式会社 濃縮パール化剤組成物
US6774095B2 (en) * 2001-05-24 2004-08-10 Kao Corporation Detergent composition
EP4299708A1 (de) * 2022-06-27 2024-01-03 The Procter & Gamble Company Flüssige handgeschirrspülmittelzusammensetzung

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3932296A (en) * 1973-05-29 1976-01-13 The Dow Chemical Company Corrosion inhibitor
US4370174A (en) * 1981-08-31 1983-01-25 Braithwaite Jr Charles H Method for removing adhesive residues with an emulsion cleaner
EP0670886A1 (de) 1992-11-30 1995-09-13 The Procter & Gamble Company Polyhydroxyfettsäureamid, sulphiertes polyhydroxyfettsäureamid und seife enthaltende waschmittelzusammensetzungen
JP3515800B2 (ja) * 1993-12-29 2004-04-05 川研ファインケミカル株式会社 ポリオキシエチレン脂肪酸アミド硫酸エステル塩型界面活性剤、該界面活性剤の製造方法および洗浄剤組成物
US5534265A (en) 1994-08-26 1996-07-09 The Procter & Gamble Company Thickened nonabrasive personal cleansing compositions
JPH09137190A (ja) * 1995-11-16 1997-05-27 Kao Corp 洗浄剤組成物
WO1997044434A1 (en) 1996-05-17 1997-11-27 The Procter & Gamble Company Low moisture laundry detergent bar with improved bleach stability
WO1998000507A2 (en) 1996-06-28 1998-01-08 The Procter & Gamble Company Nonaqueous detergent compositions containing bleach precursors
JPH10339783A (ja) 1997-04-09 1998-12-22 Seiko Epson Corp 電子時計
JPH10330783A (ja) * 1997-06-02 1998-12-15 Lion Corp 洗浄剤組成物
JP3844391B2 (ja) 1997-12-19 2006-11-08 電気化学工業株式会社 モルタル又はコンクリート部材の製造方法

Also Published As

Publication number Publication date
DE60034215T2 (de) 2007-12-20
CN100372919C (zh) 2008-03-05
WO2001040421A1 (fr) 2001-06-07
CN1339059A (zh) 2002-03-06
EP1149892A1 (de) 2001-10-31
US20010034310A1 (en) 2001-10-25
DE60034215D1 (de) 2007-05-16
US6407054B2 (en) 2002-06-18
EP1149892A4 (de) 2004-06-02

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